MXPA03008117A

MXPA03008117A - Derivados heterociclicos para el tratamiento del cancer y otras enfermedades proliferativas.

Derivados heterociclicos para el tratamiento del cancer y otras enfermedades proliferativas.

Info

Publication number: MXPA03008117A
Authority: MX; Mexico
Prior art keywords: substituted; adamantyl; residue; thiazolidinedione; phenyl
Prior art date: 2001-03-07

Application number

MXPA03008117A

Other languages

English (en)

Spanish (es)

Inventor

B Ibarra Jason

Original Assignee

Incyte San Diego Inc

Priority date

2001-03-07

Filing date

2002-03-07

Publication date

2004-11-12

2002-03-07 Application filed by Incyte San Diego Inc filed Critical Incyte San Diego Inc

2004-11-12 Publication of MXPA03008117A publication Critical patent/MXPA03008117A/es

Links

125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 73
238000011282 treatment Methods 0.000 title claims abstract description 49
206010028980 Neoplasm Diseases 0.000 title claims abstract description 45
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 24
201000010099 disease Diseases 0.000 title claims abstract description 23
201000011510 cancer Diseases 0.000 title claims abstract description 16
230000002062 proliferating effect Effects 0.000 title description 3
125000003118 aryl group Chemical group 0.000 claims abstract description 93
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 93
125000000217 alkyl group Chemical group 0.000 claims abstract description 64
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 48
239000001257 hydrogen Substances 0.000 claims abstract description 45
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 44
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 41
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 30
125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 29
150000003839 salts Chemical class 0.000 claims abstract description 24
229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
-1 tetrahydro-2-naphthyl Chemical group 0.000 claims description 264
150000001875 compounds Chemical class 0.000 claims description 168
125000004432 carbon atom Chemical group C* 0.000 claims description 62
125000001424 substituent group Chemical group 0.000 claims description 46
125000005431 alkyl carboxamide group Chemical group 0.000 claims description 39
125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 38
150000002431 hydrogen Chemical group 0.000 claims description 25
229940123464 Thiazolidinedione Drugs 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000005415 substituted alkoxy group Chemical group 0.000 claims description 18
125000004438 haloalkoxy group Chemical group 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
239000008194 pharmaceutical composition Substances 0.000 claims description 13
125000000304 alkynyl group Chemical group 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
150000002825 nitriles Chemical class 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
125000005017 substituted alkenyl group Chemical group 0.000 claims description 10
125000004426 substituted alkynyl group Chemical group 0.000 claims description 10
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 7
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
230000004663 cell proliferation Effects 0.000 claims description 4
239000005977 Ethylene Substances 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
LLJRXVHJOJRCSM-UHFFFAOYSA-N 3-pyridin-4-yl-1H-indole Chemical group C=1NC2=CC=CC=C2C=1C1=CC=NC=C1 LLJRXVHJOJRCSM-UHFFFAOYSA-N 0.000 claims description 2
IXXKNSSOLZTGKV-UHFFFAOYSA-N 5-[6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalen-2-yl]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)C(OC)=CC=C1C(C=C1C=C2)=CC=C1C=C2C1SC(=O)NC1=O IXXKNSSOLZTGKV-UHFFFAOYSA-N 0.000 claims description 2
CLYLAPYROSOQCD-UHFFFAOYSA-N 5-[[4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)C(O)=CC=C1C(C(=C1)Cl)=CC=C1C=C1SC(=O)NC1=O CLYLAPYROSOQCD-UHFFFAOYSA-N 0.000 claims description 2
CNNYFRAGPCWVPG-UHFFFAOYSA-N 5-[[4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-fluorophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)C(O)=CC=C1C(C(=C1)F)=CC=C1C=C1SC(=O)NC1=O CNNYFRAGPCWVPG-UHFFFAOYSA-N 0.000 claims description 2
KGOQVGKERZYASH-UHFFFAOYSA-N 5-[[4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-methylphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(C=2C=C(C(O)=CC=2)C23CC4CC(CC(C4)C2)C3)C(C)=CC=1C=C1SC(=O)NC1=O KGOQVGKERZYASH-UHFFFAOYSA-N 0.000 claims description 2
GPCWZSQNXYCZPP-UHFFFAOYSA-N 5-[[4-[7-(1-adamantyl)-1,3-benzodioxol-5-yl]phenyl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound O=C1NC(=S)SC1=CC1=CC=C(C=2C=C(C=3OCOC=3C=2)C23CC4CC(CC(C4)C2)C3)C=C1 GPCWZSQNXYCZPP-UHFFFAOYSA-N 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
NACSQKPBVUDRES-UHFFFAOYSA-N 3-[5-[3-(1-adamantyl)-4-methoxyphenyl]naphthalen-1-yl]-5-methylidene-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)C(OC)=CC=C1C(C1=CC=C2)=CC=CC1=C2N1C(=S)SC(=C)C1=O NACSQKPBVUDRES-UHFFFAOYSA-N 0.000 claims 1
AXCVFNHYHNTRAJ-UHFFFAOYSA-N 3-[6-[3-(1-adamantyl)-4-hydroxyphenyl]naphthalen-2-yl]-5-methylidene-1,3-thiazolidine-2,4-dione Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)C(O)=CC=C1C(C=C1C=C2)=CC=C1C=C2N1C(=O)SC(=C)C1=O AXCVFNHYHNTRAJ-UHFFFAOYSA-N 0.000 claims 1
GTCRBMMHDZQTOA-UHFFFAOYSA-N 5-[[4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-ethoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C=1C=C(C=2C=C(C(O)=CC=2)C23CC4CC(CC(C4)C2)C3)C(OCC)=CC=1C=C1SC(=O)NC1=O GTCRBMMHDZQTOA-UHFFFAOYSA-N 0.000 claims 1
AFPFWHRROKCCHV-UHFFFAOYSA-N 5-[[4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-nitrophenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)C(O)=CC=C1C(C(=C1)[N+]([O-])=O)=CC=C1C=C1SC(=O)NC1=O AFPFWHRROKCCHV-UHFFFAOYSA-N 0.000 claims 1
150000002391 heterocyclic compounds Chemical class 0.000 abstract description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 142
239000000203 mixture Substances 0.000 description 124
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 114
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 103
238000005481 NMR spectroscopy Methods 0.000 description 86
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
239000007787 solid Substances 0.000 description 70
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 70
239000000243 solution Substances 0.000 description 67
238000000034 method Methods 0.000 description 62
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
235000019439 ethyl acetate Nutrition 0.000 description 55
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 49
239000012267 brine Substances 0.000 description 48
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 44
238000010992 reflux Methods 0.000 description 42
210000004027 cell Anatomy 0.000 description 40
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 38
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 38
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
239000000741 silica gel Substances 0.000 description 34
229910002027 silica gel Inorganic materials 0.000 description 34
239000012300 argon atmosphere Substances 0.000 description 33
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
239000000725 suspension Substances 0.000 description 32
239000010410 layer Substances 0.000 description 28
229910052943 magnesium sulfate Inorganic materials 0.000 description 27
235000019341 magnesium sulphate Nutrition 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 26
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 26
239000000543 intermediate Substances 0.000 description 24
ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical group O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 23
239000003480 eluent Substances 0.000 description 23
229910052786 argon Inorganic materials 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 20
239000000460 chlorine Substances 0.000 description 19
238000005859 coupling reaction Methods 0.000 description 19
229910052799 carbon Inorganic materials 0.000 description 18
150000003254 radicals Chemical class 0.000 description 18
230000002829 reductive effect Effects 0.000 description 18
150000005347 biaryls Chemical group 0.000 description 17
239000002904 solvent Substances 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
239000012044 organic layer Substances 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
238000012360 testing method Methods 0.000 description 16
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 15
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000010168 coupling process Methods 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 14
230000008878 coupling Effects 0.000 description 14
229910052736 halogen Inorganic materials 0.000 description 13
150000002367 halogens Chemical class 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
150000001987 diarylethers Chemical class 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 11
206010061902 Pancreatic neoplasm Diseases 0.000 description 11
208000015486 malignant pancreatic neoplasm Diseases 0.000 description 11
201000002528 pancreatic cancer Diseases 0.000 description 11
208000008443 pancreatic carcinoma Diseases 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
150000001299 aldehydes Chemical class 0.000 description 10
125000002947 alkylene group Chemical group 0.000 description 10
230000001093 anti-cancer Effects 0.000 description 10
239000002246 antineoplastic agent Substances 0.000 description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 10
238000001727 in vivo Methods 0.000 description 10
239000001301 oxygen Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
239000000047 product Substances 0.000 description 10
210000004881 tumor cell Anatomy 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
229910052794 bromium Inorganic materials 0.000 description 9
239000011203 carbon fibre reinforced carbon Substances 0.000 description 9
238000001914 filtration Methods 0.000 description 9
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
238000003756 stirring Methods 0.000 description 9
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
241001465754 Metazoa Species 0.000 description 8
150000001543 aryl boronic acids Chemical class 0.000 description 8
150000001502 aryl halides Chemical class 0.000 description 8
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
DLLDUYJRQNTEOR-UHFFFAOYSA-N 6-bromonaphthalene-2-carbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(Br)=CC=C21 DLLDUYJRQNTEOR-UHFFFAOYSA-N 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
238000009833 condensation Methods 0.000 description 7
230000005494 condensation Effects 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
125000005842 heteroatom Chemical group 0.000 description 7
150000002576 ketones Chemical class 0.000 description 7
150000004714 phosphonium salts Chemical class 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 6
NYJXKHIVLGWPCF-UHFFFAOYSA-N 2-(1-adamantyl)-4-bromophenol Chemical compound OC1=CC=C(Br)C=C1C1(C2)CC(C3)CC2CC3C1 NYJXKHIVLGWPCF-UHFFFAOYSA-N 0.000 description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
108091003079 Bovine Serum Albumin Proteins 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
241000282412 Homo Species 0.000 description 6
125000004423 acyloxy group Chemical group 0.000 description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
230000004071 biological effect Effects 0.000 description 6
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 6
150000003857 carboxamides Chemical class 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
239000012894 fetal calf serum Substances 0.000 description 6
239000012634 fragment Substances 0.000 description 6
150000004820 halides Chemical class 0.000 description 6
238000000338 in vitro Methods 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
239000000126 substance Substances 0.000 description 6
125000004001 thioalkyl group Chemical group 0.000 description 6
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 6
CWOXRESXYUACGJ-UHFFFAOYSA-N 6-(3-tert-butyl-4-methoxyphenyl)naphthalene-2-carbaldehyde Chemical compound C1=C(C(C)(C)C)C(OC)=CC=C1C1=CC=C(C=C(C=O)C=C2)C2=C1 CWOXRESXYUACGJ-UHFFFAOYSA-N 0.000 description 5
CNWWYFCUMSSILQ-UHFFFAOYSA-N 6-[4-methoxy-3-(1-methylcyclohexyl)phenyl]naphthalene-2-carbaldehyde Chemical compound COC1=CC=C(C=2C=C3C=CC(C=O)=CC3=CC=2)C=C1C1(C)CCCCC1 CNWWYFCUMSSILQ-UHFFFAOYSA-N 0.000 description 5
206010006187 Breast cancer Diseases 0.000 description 5
208000026310 Breast neoplasm Diseases 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 description 5
125000003710 aryl alkyl group Chemical group 0.000 description 5
235000019445 benzyl alcohol Nutrition 0.000 description 5
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
125000001183 hydrocarbyl group Chemical group 0.000 description 5
239000000463 material Substances 0.000 description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
230000035755 proliferation Effects 0.000 description 5
KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
HVKCYFMVDCASDE-UHFFFAOYSA-N 2-[6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalen-2-yl]-2-chloroacetonitrile Chemical compound C1=C(C(Cl)C#N)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 HVKCYFMVDCASDE-UHFFFAOYSA-N 0.000 description 4
PBVKCABKORQRAV-UHFFFAOYSA-N 3-[6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalen-2-yl]-5-methylidene-1,3-thiazolidine-2,4-dione Chemical compound C1=C(C23CC4CC(CC(C4)C2)C3)C(OC)=CC=C1C(C=C1C=C2)=CC=C1C=C2N1C(=O)SC(=C)C1=O PBVKCABKORQRAV-UHFFFAOYSA-N 0.000 description 4
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